Sodium Hydroxide → HCID 57955572, compound

HRID 914215Notes

Reaction equation

HRID 914215 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:37]=[CH:36][C:25]([C:26]([NH:28][CH:29]5[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]5)=[O:27])=[CH:24][C:23]=4[O:38][CH3:39])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:40].[Na+]>CN(C=O)C>[CH:1]1([N:6]([C:7]2[C:8]([NH:9][CH3:16])=[CH:17][N:18]=[C:19]([NH:21][C:22]3[CH:37]=[CH:36][C:25]([C:26](=[O:27])[NH:28][CH:29]4[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]4)=[CH:24][C:23]=3[O:38][CH3:39])[N:20]=2)[CH2:12][C:11]([F:14])([F:13])[C:10]([OH:40])=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 25015677Ro3280

Product 1

HCID 57955572HCID 57955572, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide (543 mg, 1 mmol) in 10 ml of DMF, was added 1N NaOH (5 ml) dropwise. The reaction mixture was stirred at rt. for 1 h and then subjected to reverse phase HPLC purification using basic column. The final compound was obtained by lyophilization first and then dried in the vacuum oven at 60° C. for 3 d (380 mg, 68%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47-1.99 (m, 12H) 2.54 (d, J=2.8 Hz, 2H) 2.64-2.79 (m, 5H) 3.00 (d, J=4.6 Hz, 2H) 3.85-4.10 (m, 6H) 4.20 (d, J=7.3 Hz, 1H) 7.42 (s, 2H) 7.48 (d, J=8.3 Hz, 1H) 7.61-7.80 (m, 1H) 8.23 (br. s., 1H) 8.42 (d, J=8.3 Hz, 1H). [M+H] calc'd for C27H37F2N7O4, 562. found 562.

Workup

  1. customphase HPLC purification

Sources & evidence

ORD record
ord-0930219e474341ff9632fdeb86082655
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

Loading…